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Tuesday, January 22, 2013

The Bet - Chapter 59 (Monday – week 9 Part 1 of 5)

The Bet

By Karen Singer

Chapter 59 (Monday – week 9 Part 1 of 5)

His sexual need
was all he could think about.Even in
his dream he could feel the dildo sliding sensually in and out of his
backside.In and out.In and out.Delicious!But he was still
frustrated.While the dream toy felt
incredibly good, it didn’t give him the fulfillment he really needed.He pulled the toy out and picked up another
one – the one Cassie used on him.In and
out.In and out.It felt so different than the one from Mel
that he had used just before.But again,
this toy wasn’t going to give him what he needed either.

His dream-self
thought again about his regular male appendage.But that was totally useless now.Totally!In his dream, he wasn’t
even wearing the darn chastity device.He could touch it if he wanted to… but he didn’t.What would be the point?It no longer functioned.It no longer gave him the release he
wanted.

He was a sissy,
and as such, normal sex as a male was no good for him anymore.He had been changed.Cursed!Reduced!Because he was a sissy,
he was no longer allowed to pleasure himself with his penis anymore… and as
such, he never even thought about getting pleasure that way… not anymore.Instead, his backside now yearned
continuously for the stimulation he had come to realize would be his only means
to fulfillment.No sex as a male every
again!The only way he could receive
pleasure was to be penetrated… not to penetrate.More like a woman than a man.But the truth was… it was not sex like a
woman… it was sex for a sissy.

Denied!Cursed!Reduced!And the intense feelings
and emotions about it drove him continuously in his dream in search of anything
that would grant him the release he so desperately wanted.

Music and talking
found their way into his dream... disturbing it… disturbing him… irritating
him… to the point where he had to wake up to acknowledge the commercial that
was now playing from his pink clock radio.He opened his eyes.It was
another day.Another day that would be
full of sissy humiliation.But his brain
also realized something else.Today
would be different.Today was Monday and
he wasn’t going to work today.

That thought
quickly led him to wonder… and worry… about what Mel had planned for him
today.She had said last night before he
left her apartment that he should get there a little early today.Why?What did she have planned?He
knew she didn’t go into her office as early as he usually went to work, so what
was going on?Only one way to find out –
he would have to go over to her apartment and wait till she told him what was
going on.Which was exactly what he
would have to do anyway.There was no
getting around it.

He rolled off of
his blow-up mattress and onto his knees, knocking over one of the empty baby
bottles near his bed.He reached up and
turned his radio off.Even on his knees,
his legs were splayed wide apart because of the heavy super thick bulk of all
the diapers he was wearing.He didn’t
even have to think about it to know he was not only soaked, but messy as
well.Struggling to his feet, he felt
the breast forms that were glued to his chest pull a little bit.The bra he was wearing helped to support them
and helped to keep them from pulling worse, but he could still feel them.

Wide leggedly, he
waddled out to his kitchen.He was again
disappointed to not see a note on his counter from Mel.Unfortunately, they were past that point
now.He went directly to his
refrigerator and pulled out three of the baby bottles he had stocked in there
yesterday.He carried them as he always
did out to his one and only chair that faced his wall of shaming pictures.

He rarely really
noticed those pictures anymore, but today he looked at them more closely.It was amazing how much they looked like a
real child had done them… scribbled them.Scribbling that didn’t even stay in the lines… colors that were all
wrong.Childish!And yet it was he who had colored them that
way – out in public – out in the restaurants!

His eyes glanced
down the wall further and fell on the plans that Sandy had drawn up for his apartment if he
lost.Plans that would essentially turn
his entire apartment into one big girly nursery.As he looked at those plans, he again felt a
twinge of sexual need stirring within him.But as usual, he was forced to ignore that need.There was nothing he would be capable of
doing about it.Part of him was
horrified by what those plans would mean if they got carried out… but an equal
part of him yearned for it just as much.He was a sissy.There was no
denying it, or the sexual need the thought of such a life brought to him.

That need did
remind him though about the new reward system that Mel had instituted
yesterday.He had been allowed to play
with one of Mel’s toys in his backside for a few minutes.But he had been forced to do it to himself
while she watched.And most
disappointingly, he had only been able to do it for a very few minutes.He remembered vowing to try to do better
today to leak before the hour and a half point whenever possible.That would rack up more minutes for him to
play.And the best way he could do that?He was already doing it – drinking from his
bottle… bottles!The more the
better!

Maybe tonight he could actually play with
himself long enough to succeed!Long
enough to achieve an orgasm!He
seriously doubted it, but it was a goal he couldn’t get out of his mind.

“No!No!No!”Mel screamed as she again
shoved at Ray’s big body.“Get
out!”He went… again, and again she
worried that he would come back.He had
been doing that over and over.She would
throw him out, and he would come back again.And it was all she could do to keep Ray and Derek from fighting with
each other.

Money, money,
money!That was all Ray wanted!And she suspected that Derek was only
interested in her money as well.She had
to protect it.She had to keep both of
them from finding out how rich she really was.But she wanted them both.Both of
them!Each of them were big strong
handsome hulking men!And as aggravating
as each of them were, it felt so good to be out with them – either of them… or
both of them as she really wanted.But
it seemed now that all they were interested in was her money.Neither of them loved her for herself.

“Are you rich?”
Derek asked in her dream.“Get out!” she
yelled at him too.Then she ran for the
safety of her bedroom.Sissy was there
with her.She sat down on her bed and he
was instantly by her side… holding her… comforting her.He alone wasn’t interested in her money.He alone didn’t make any demands of her.He alone was the one she controlled –
completely!

And even in her
dream, she remembered that was part of her problem – her usual problem with
men.All men!She liked being in control too much.It was all she could do sometimes to play the
little Miss Muffin submissive woman that they all seemed to expect from
her.But she was more than that.Much more.She was smart!She was
powerful!Very powerful! She yearned to
display that power… yet the only one she really controlled was Sissy.At least he didn’t make any demands of her
she didn’t like.He wasn’t allowed!

In her dream, her
bedroom door nearly exploded as Ray kicked it in.He was back again!“Are you rich?” he demanded.

“No!No!No!Get out!” she yelled once
again!

And then Derek
was there.“Are you rich?” he demanded
as well.

“Get out!” she
yelled at him too.But neither of them
left.They didn’t love her for herself,
they only wanted her money!“Get out!”
she yelled again as she felt her dream tears falling.“Get out!Get out!Get out!”But each repetition of the words came with
less and less intensity.In her self-pity,
she finally collapsed on the bed… and Sissy held her in his arms.

“It’s all
right,” Sissy said to her over and over again as she cried.“It’s all right.”

The annoying
buzzing of her alarm clock forced its way into her dream, pulling her out of it.It removed all memory of what she had been
dreaming about, but not the emotions of the dream.She opened her eyes only knowing that she had
been upset and crying in her dream, nothing more.She took a deep breath to try to calm
herself.It was just a dream.Just a dream – whatever it was that she had
been dreaming about.

She rolled over
and realized that she smelled fresh coffee brewing.Sissy!Once again Sissy was out there as he should be… her morning coffee was
ready and waiting!Perfect!Perfect!Perfect!

Chad was concentrating on how wet
his diaper might be when he heard Mel calling from her bedroom.His diaper certainly wasn’t wet enough to be
leaking yet, but then he had only had it on for a little over an hour now.Still plenty of time to go.Her voice calling his name – his sissy name –
galvanized him into action.Forgetting
about his wet diaper, he quickly poured her a fresh cup of coffee and hurried
with it into her bedroom.She was
sitting up on her bed… smiling at him, he was happy to see.He curtseyed, careful not to spill the
coffee.“Good morning, Mistress,” he
said in his stupid, silly sissy voice.Then he carefully curtseyed again.

“Good morning
Sissy,” Mel returned as she looked him over carefully.As she hoped, he was attired perfectly in his
maid’s uniform again.She took the
offered cup of coffee and sipped at it.Mmm.So good!And she didn’t even have to get out of bed to
brew it or pour it into the cup.Sissy
had done all that for her and brought it to her only moments after she had
called his name.Perfect!Perfect!Perfect!“Thank you, Sissy,” she
said with a bit of a smile.“I’ll just
have a couple of pieces of toast for breakfast this morning.Oh, and put some strawberry jam on it as
well.And I’ll have it right here in
bed.”

Chad curtseyed and hurried out of
the room.An easy breakfast to
prepare.A moment later, he was loading
bread into her toaster.

The coffee helped
kick start Mel’s brain to thinking.Thoughts of how nice it was to finally have Sissy there and doing what
she wanted him to be doing were interrupted by thoughts of her day ahead –
specifically, the meeting with Feinbaum’s group over the contract.Even now, after having been through the
contract so carefully, there was still something that bothered her about
it.And yet, she could find no fault at
all with the thing.The contract was a
massive piece of legal art… constructed by one of the best in the
business.And today they would be
meeting with Green Growers to recommend that they sign the thing and finalize
it tomorrow.Hopefully, she would merely
be attending and wouldn’t have to even open her mouth there.What would she say anyway?

This contract had
come along at the wrong time!It was seriously
distracting her from what she needed to be doing with Sissy.She had mostly cleared her schedule for all
this week just so she could work closely with Sissy and make sure she would win
the bet, but there had simply been no getting around this deal.You don’t say no to Old Man Feinbaum!

So what was she
going to do with Sissy today?Her
thoughts were interrupted by him coming back into the room bearing a tray with
a plate and two pieces of toast covered in strawberry jam.She let him place the tray on her lap, then
she handed him her coffee cup to refill.As he hurried off, she went back to her planning.What to do with Sissy?Obviously, the best thing she could do with
him today would be to take him into work with her and leave him with Andrea
till she could get out of that meeting.Then she would be free for the rest of the day to do what she liked with
him… or to him as the case might be.She
actually giggled a bit at the thought.

She was still
giggling to herself as he came back in with the fresh cup of coffee.“Have you leaked at all yet?” she asked him
as he curtseyed and offered the cup to her.

Chad curtseyed again.“Not yet,” he replied in his silly voice,
“but I still have plenty of time.”Curtsey.

“How much time?”

He looked at the
clock beside her bed.Curtsey.“About twenty minutes yet.”Curtsey.

“So in five more
minutes your chance of gaining some reward time will expire,” she stated.

Mel was glad to
hear that.“How many bottles have you
finished so far this morning?”

Curtsey.“I’m working on number six,” he replied.Curtsey.

“So I take it
you’re trying hard to rack up some of that reward time.”

Curtsey.“Very hard!”Curtsey.

Mel was
pleased.Very pleased.It was exactly what she had hoped for…
exactly what she wanted to hear.Hopefully, the little bit of reward he might gain every day would keep
him trying harder and harder to continuously wet himself – and in the process,
would keep robbing him of any ability he might still have to hold back and
control himself.Hopefully!

“Very good,
Sissy,” she replied.“I’m glad to hear
that.And I hope you manage to gain a
lot of reward time today.”She switched
subjects… somewhat.“Have you eaten
anything yet this morning?”

Curtsey.“No, Mistress.”Curtsey.

“Good!You’re not supposed to!” she replied
authoritatively.“Now go start making
your breakfast while I’m eating.I’m
sure you know by now what you’re allowed to have.I’ll be in soon to set you up in your
highchair with it.”She watched as he
curtseyed and hurried off.Yes, despite
having to still worry about taking care of him and making him incontinent, it
was going to be so great when this bet was over with and he would be locked
into her service.Then, all she had to
do would be to find a way to make it permanent.Unfortunately, her thoughts were clouded with the one thing she didn’t
want to think about concerning Sissy… the one thing she still hadn’t found an
answer to yet – self-respect, friends, and a life!

Chad had already finished heating
his baby cereal and had poured it into one of his childish bowls by the time
Mel came out of her bedroom – wearing nothing but her nightgown with a light
robe over it.She saw that he had his
breakfast ready, but her first concern was his diaper.“Are you leaking yet?” she asked, knowing
that the deadline for any possible reward was only a little over a minute
away.

Chad quickly took a moment to try
to figure out if he might be leaking.Then he curtseyed.“I don’t think
so,” he replied uncertainly.“But I have
to be very close.”Then he curtseyed
again.

Chad was disappointed, he had been
really trying since he had gotten out of bed.He wanted that reward time – and technically, he did still have a few
minutes left.Reluctantly, he headed for
his highchair, but he stopped just as he turned around and started to climb up
into it.He looked up at Mel
hopefully.“It’s possible that I might
be leaking now,” he told her without bothering to curtsey.“Or if not… I could be very soon.If I get up into the chair, I might not be
able to tell.”

“Lift your
dress,” she told him.“Let’s see.”

Chad pulled his skirt up high and
started feeling around the leg openings of his diaper while Mel looked on
closely.

“I don’t see
anything yet,” Mel said.“But you do
look awfully wet.”

“I know I’m
really close!” Chad
insisted.

Mel shook her
head.“Okay Sissy.Grab your bottle.”She glanced at the clock.“You’ve got thirty seconds.If you’re not leaking by then, then you’ll
just have to start your breakfast and hope that you’re leaking before the next
fifteen minutes gets through.Otherwise
I’m going to paddle you good!”

As wet as his
diaper was, Chad
was sure he would be leaking before his second deadline.What he wanted though was to be leaking in
the next few seconds.He attacked his
bottle furiously, sucking as hard as he could on it while Mel watched.Twenty seconds later, he felt himself peeing
again.As always, it was only a tiny
bit, but it was more added to his diaper.Still drinking from his bottle, he began feeling around the bottom of
his diaper again.Leak!Leak!Leak!

He glanced at the
clock.Ten more seconds!Please pee again!Please leak!The time was ticking down.Leak!Leak!And he thought he felt something moist at the
bottom of his diaper!“I’m leaking!” he
proclaimed quickly.

Mel glanced at
the clock and saw it ticking down the final few seconds.With somewhat of a smirk on her face, she
said, “It’s so close I shouldn’t give you anything at all.But you tried so hard, I’ll grant you a whole
minute – this time.Don’t expect me to
be so lenient again!”

Chad didn’t care.He had done it.He had gotten his diaper leaking ahead of
time and now had one whole minute of reward time coming.

“By the way,” Mel said to him.“You might want to get that diaper changed
pretty fast.I started your time running
the minute you told me you were leaking.”

Once Chad’s
diaper was changed, Mel locked him into his highchair and left him not only with
his usual breakfast and baby bottle, but she also set out two more bottles for
him to drink.“That’s just to give you
something to work on while I’m getting dressed,” she told him.Then she left him alone knowing he wasn’t
going anywhere till she came back to release him.

Now, what was she
going to wear for this meeting?It was a
foregone conclusion that she would be wearing one of the two new suits she had
just bought.But which one?She considered that while she showered and
did her hair.She was still considering
it as she did most of her makeup.In the
end, she wore the same blue suit she had worn to the last meeting.Since the room had been full of men, she
doubted that anyone there would really remember what she had worn anyway.

Websites

About Me

For those of you who might remember me, I’m the same Karen who used to have the website My Sissy Rules Fantasy that Yahoo suddenly deleted several years ago. I still miss my website and really hope to have one back again someday, but, well, I guess I procrastinate a lot – plus, I think the internet has been doing a lot of growing lately.
Other than that, what else can I tell you about me? As I said, I’m male. An older male to be exact. One who has wished very hard his entire (and I mean entire) life that he had been born a girl. Seriously! You have no idea how much that aches in me – always.
I’ve always been small and skinny, except recently my stomach has decided it wants to be large and fat (Arrgh!). Oh yeah, I’m also very married to a wonderful woman who knows nothing at all about this side of me… and I intend to work very hard at keeping it that way.
So for me, life is good, and life is bad, and life is worse, and life is horrible, and life is great. But that’s what life is – you take what it hands you and you do the very best you can under the circumstances. And you enjoy what little bits that you can, wherever and however you can manage it.